Pyridine → 4-(Chloromethyl)-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]benz amide

HRID 587832Notes

Reaction equation

HRID 587832 reaction equation
[CH2:1]([C:3]1[CH:9]=[C:8]([C:10]([F:19])([C:15]([F:18])([F:17])[F:16])[C:11]([F:14])([F:13])[F:12])[CH:7]=[C:6]([CH3:20])[C:4]=1[NH2:5])[CH3:2].N1C=CC=CC=1.[Cl:27][CH2:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1>O1CCCC1.CN(C)C1C=CN=CC=1.O>[Cl:27][CH2:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([NH:5][C:4]2[C:6]([CH3:20])=[CH:7][C:8]([C:10]([F:19])([C:11]([F:14])([F:13])[F:12])[C:15]([F:16])([F:17])[F:18])=[CH:9][C:3]=2[CH2:1][CH3:2])=[O:34])=[CH:31][CH:30]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 701364-(Chloromethyl)benzoyl chlorideHCID 227346102-Methyl-6-ethyl-4-(heptafluoro-prop-2-yl)-aniline

Product 1

HCID 866666154-(Chloromethyl)-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]benz amideYield 82.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylaniline (0.50 g) and pyridine (0.20 g) were dissolved in tetrahydrofuran (10 ml). To the solution, 4-(chloromethyl)benzoyl chloride (0.33 g) and 4-dimethylaminopyridine (0.02 g) were added and the mixture was refluxed under heating for 3 hours. After adjusting to room temperature, the reaction solution was diluted with water and extracted twice with ethyl acetate. The organic phases were combined, washed with 2N hydrochloric acid and dried over Mg(SO4). After filtering off the drying agent, the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was washed with hexane to obtain 4-(chloro methyl)-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoro-propan-2-yl)-6-methylphenyl]benzamide (0.62 g, yield 74%).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 3 hours
  3. customAfter adjusting to room temperature
  4. extractionextracted twice with ethyl acetate
  5. washwashed with 2N hydrochloric acid
  6. dry with materialdried over Mg(SO4)
  7. filtrationAfter filtering off the drying agent
  8. distillationthe solvent was distilled off under reduced pressure
  9. customto obtain a crude product
  10. washThe crude product was washed with hexane

Sources & evidence

ORD record
ord-cb705faad3664c69b6309df2830c91c0
Source dataset
uspto-grants-2016_01
Patent number
US09227923B2

Reaction notes

Loading…